Cosby was rich and famous by 1966 and immensely popular in America, he wasn’t born or raised in the deep South, he is from Philadelphia.
So? what about the 1950’s? He was exactly living large then, and he didn’t confirm himself to only integrated areas. Even in 1966 there were places like hotels he was not welcome.
Prejudice wasn’t limited to the deep south. When my Mom was growing up in Indiana (20s, 30s), it was illegal in her county for a black man to be there overnight. She thought they changed the law when she was in her early teens.
16 states had anti-miscegenation laws overturned in 1967. Indiana repealed theirs in 1965. Cosby enlisted in the Navy in 1956.
“Cosby won awards running on the Navy track team, but also experienced racial discrimination, being forced to eat in the kitchen of cafes where the team stopped to eat while on the road. He was honorably discharged after four years of service in 1960.”